Winona Insider View: Top 5 Hiking Spots


By: Sydney Bockelman and Alexa Shapiro, Winonans and Outdoor Enthusiasts

The beautiful bluffs surrounding Winona provide us with ever-changing views and activities for each season. One of our favorite ways to explore the bluffs is on foot–hiking, walking, or trail running.

If you like the idea of spending a morning walking among the trees and gazing at the Mighty Mississippi or an evening hike along the blufftops guided by the light of the moon–Winona is the place for you to explore!

With so many trails and ways to get outside, it can be overwhelming to know where to get started or which hiking trails you should check out. The Winona Outdoor Collaborative, a local non-profit, focuses on creating a more inclusive and welcoming outdoors for all people through  free monthly meet-ups, quarterly workshops, and guided trips. Additionally, the organization will offer low-cost outdoor equipment rentals in the near future.

The Collaborative put together this guide featuring the organization’s top 5 hikes in the Winona area!

  1. Sugarloaf Hike

The trailhead is located behind Edina Realty on East Lake Boulevard, with parking available on either side of the road (no parking in the Edina Realty or neighboring business parking lots).

This hike begins with a climb up into the bluffs, with a wide trail system that has plenty of pace to stop and take in the view or catch your breath. The trail will take you all the way to the base of Sugarloaf. No climbing is allowed on Sugarloaf itself without proper rock climbing equipment.

  1. Holzinger Trails High to Low Rollers

After parking in the designated lot, you’ll head toward the trailhead sign located on the right hand side of the parking lot. The trail will follow the base of the bluffs, weaving around the Woodlawn Cemetery and eventually looping you back to the parking lot.

  1. Aghaming Park

Parking is located alongside the trail system, right past the Wagon Bridge. The hike is located on the right hand side of the road, just past the Wagon Bridge on Latsch Island. A sign will show you the trailhead. In the spring, the trail may be flooded.

  1. Perrot State Park: Brady’s Bluff

A Wisconsin State Park vehicle permit is required for this hike (day passes are $11 or annual passes are $38 for MN residents), however the trails and views in this park are worth it. There are over 12 miles of trails in the park, however we recommend Brady’s Bluff hike which overlooks the Mississippi River and gives glimpses of Winona.

  1. Trempealeau Refuge: Delta Point Hike

This hike is located off of the Great River Road/35 in Wisconsin near Trempealeau, just past the railroad tracks in Marshland. Use this pin on Google Maps to find the location. There is a small parking lot and the trail begins right at the edge of the lot.

Feeling inspired? Register now for Winona Outdoor Collaborative’s 24-Hike Series. Through this free program, participants will sign a commitment pledge to go on 24 hikes in the Winona area throughout the year. Participants receive access to the Collaborative’s recommended 24 hikes, however any hike within 40 miles of Winona counts. Participants can hike any length of time – so long as you’re getting outdoors and moving in nature, it counts! Participants will also be eligible for a series of prizes throughout the year and, upon completion of the hike series, will receive a sticker.

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